bis(2-naphthylmethylthio)acetylene | 210626-03-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: bis(2-naphthylmethylthio)acetylene
• 英文别名: 2-[2-(Naphthalen-2-ylmethylsulfanyl)ethynylsulfanylmethyl]naphthalene
• CAS: 210626-03-2
• 化学式: C₂₄H₁₈S₂
• 分子量: 370.539
• InChiKey: UXDQNTATXGGSEE-UHFFFAOYSA-N

物化性质

• 熔点：
  128-129 °C(Solv: ethanol (64-17-5))
• 沸点：
  578.0±53.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  bis(2-naphthylmethylthio)acetylene 在 一氯化碘 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.17h， 以55%的产率得到2-iodo-1-(naphthalen-2-ylmethylsulfanyl)-4H-benzo[f]isothiochromene
  参考文献：
  名称：

  Versatile Route to Functionalized 1H-2-Benzothiopyrans and 1H-2-Naphthothiopyrans by Electrophilic Cyclization of Bis(arylmethylthio)acetylenes:  2-Benzo- and 2-Naphthothiopyrylium Salts

  摘要：

  Substituted 1H-2-benzothiopyrans find applications as pharmaceutically active compounds or synthons for more complex sulfur heterocycles. However, restricted variability in their synthesis limits the application for research or industrial purposes. To develop a direct and fast route to substituted and functionalized 1H-2-benzothiopyrans, we investigated the ring closure of symmetrical bis(arylmethylthio)acetylenes with iodine monochloride or bromine. This facile reaction yielded 1H-3-halo-4-arylmethylthio-2-benzo- and 2-naphthothiopyrans via postulated vinyl cations in yields of 47-86%. Substituted 2-benzo- and 2-naphthothiopyrylium salts were prepared by hydride abstraction with triphenylcarbenium tetrafluoroborate from the products, further enhancing the synthetic potential of the found cyclization reaction.

  DOI：

  10.1021/jo972334l
• 作为产物：
  描述：

  2-溴甲基萘 在 氨 、 sodium 、 silica gel 作用下， 反应 16.5h， 生成 bis(2-naphthylmethylthio)acetylene
  参考文献：
  名称：

  Versatile Route to Functionalized 1H-2-Benzothiopyrans and 1H-2-Naphthothiopyrans by Electrophilic Cyclization of Bis(arylmethylthio)acetylenes:  2-Benzo- and 2-Naphthothiopyrylium Salts

  摘要：

  Substituted 1H-2-benzothiopyrans find applications as pharmaceutically active compounds or synthons for more complex sulfur heterocycles. However, restricted variability in their synthesis limits the application for research or industrial purposes. To develop a direct and fast route to substituted and functionalized 1H-2-benzothiopyrans, we investigated the ring closure of symmetrical bis(arylmethylthio)acetylenes with iodine monochloride or bromine. This facile reaction yielded 1H-3-halo-4-arylmethylthio-2-benzo- and 2-naphthothiopyrans via postulated vinyl cations in yields of 47-86%. Substituted 2-benzo- and 2-naphthothiopyrylium salts were prepared by hydride abstraction with triphenylcarbenium tetrafluoroborate from the products, further enhancing the synthetic potential of the found cyclization reaction.

  DOI：

  10.1021/jo972334l

文献信息

• Versatile Route to Functionalized 1<i>H-</i>2-Benzothiopyrans and 1<i>H-</i>2-Naphthothiopyrans by Electrophilic Cyclization of Bis(arylmethylthio)acetylenes:  2-Benzo- and 2-Naphthothiopyrylium Salts
  作者：Thomas R. Klein、Marco Bergemann、Nasser A. M. Yehia、Egon Fanghänel

  DOI：10.1021/jo972334l

  日期：1998.7.1

  Substituted 1H-2-benzothiopyrans find applications as pharmaceutically active compounds or synthons for more complex sulfur heterocycles. However, restricted variability in their synthesis limits the application for research or industrial purposes. To develop a direct and fast route to substituted and functionalized 1H-2-benzothiopyrans, we investigated the ring closure of symmetrical bis(arylmethylthio)acetylenes with iodine monochloride or bromine. This facile reaction yielded 1H-3-halo-4-arylmethylthio-2-benzo- and 2-naphthothiopyrans via postulated vinyl cations in yields of 47-86%. Substituted 2-benzo- and 2-naphthothiopyrylium salts were prepared by hydride abstraction with triphenylcarbenium tetrafluoroborate from the products, further enhancing the synthetic potential of the found cyclization reaction.